Conditions | Yield |
---|---|
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 7h; | 95% |
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
With tetramethyldisilazane; isopropyl titanoate(IV) In methyl cyclohexane at 60℃; | 94% |
Conditions | Yield |
---|---|
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 47h; | 87% |
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 47h; | 87% |
1,4-dibromo-butane
chloro-diphenylphosphine
A
Tetraphenyldiphosphin
B
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide In various solvent(s) Ambient temperature; elektrochemical reaction, anode Mg bar, cathode stainless steel; var. solv.; Yields of byproduct given; | A n/a B 85% |
potassium diphenylphosphine
(S)-2-(dibenzylamino)-3-phenyl-1-bromopropane
A
1,4-di(diphenylphosphino)-butane
B
Dibenzyl-((S)-1-benzyl-2-diphenylphosphanyl-ethyl)-amine
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - -40℃; | A 30% B 64% |
1,4-dichlorobutane
sodium diphenylphosphide
A
(4-chlorobutyl)diphenylphosphane
B
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene 1) -50 deg C, 2) 50 deg C; | A 53% B n/a |
tetrachlorure d'octaphenyl-1,1,4,4,9,9,12,12 tetraphosphonia-1,4,9,12 cyclohexadecane
A
1,4-di(diphenylphosphino)-butane
B
1,4-bis(diphenylphosphinyl)butane
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 14h; Heating; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With potassium hydroxide 1.) DMSO, 20 deg C, 2.) 50 deg C, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at 0℃; for 0.5h; |
tetrachlorure d'octaphenyl-1,1,6,6,9,9,14,14 tetraphosphonia-1,6,9,14 cyclohexadecadiene-3,11
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr 2: 5N NaOH / aq. ethanol / 14 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / toluene / 4 h / Heating 2: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr 3: 5N NaOH / aq. ethanol / 14 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 80 percent / toluene / 96 h / Heating; var. conc. and time 2: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr 3: 5N NaOH / aq. ethanol / 14 h / Heating View Scheme |
Conditions | Yield |
---|---|
pentamethylcyclopentadienyliron(III) dicarbonyl dimer In toluene under N2; soln. of Ru complex and 1 equiv of ligand in toluene heated to 105-110 °C, added catalyst, completion of react. detected by IR; cooled, evapd., sepd. by chromy. (SiO2, benzene), recrystd. from toluene/hexane; elem. anal.; |
A
[RuCl2(η6-p-cymene)]2(μ-dppb)
B
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In dichloromethane-d2 at 25℃; Equilibrium constant; Inert atmosphere; Schlenk technique; |
1,4-dibromo-butane
chloro-diphenylphosphine
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
Stage #1: 1,4-dibromo-butane With iodine; magnesium In tetrahydrofuran for 3h; Inert atmosphere; Stage #2: chloro-diphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; |
1,4-di(diphenylphosphino)-butane
(1,4-bis(diphenylphosphino)butane)molybdenum tetracarbonyl
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With air In water; dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; | 100% |
(S)-(-)-2-naphthyl-3-trifluoromethanesulfonyloxybiphenyl
Diphenylphosphine oxide
1,4-di(diphenylphosphino)-butane
(S)-(+)-2-naphthyl-3-diphenylphosphinylbiphenyl
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium diacetate In dimethyl sulfoxide | 99% |
carbonylgold(I) chloride
1,4-di(diphenylphosphino)-butane
1,4-bis(diphenylphosphino)butane digold(I) dichloride
Conditions | Yield |
---|---|
In benzene byproducts: CO; soln. of Ph2PCH2CH2CH2CH2PPh2 dropped to soln. of (OC)AuCl at 20°C under dry N2, stirred for 1 h (CO removed); filtered; | 99% |
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
99% |
ethylenediamine
1,4-di(diphenylphosphino)-butane
(dppb)RuCl2(enethylenediamine)
Conditions | Yield |
---|---|
Stage #1: benzene ruthenium(II) dichloride dimer; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 120℃; for 1.5h; Stage #2: ethylenediamine In dichloromethane at 40℃; for 1.5h; | 99% |
hydrogenchloride
palladium
1,4-di(diphenylphosphino)-butane
[1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride
Conditions | Yield |
---|---|
Stage #1: hydrogenchloride; palladium With nitric acid In water Stage #2: 1,4-di(diphenylphosphino)-butane In water; N,N-dimethyl-formamide at 50℃; for 1h; | 98.9% |
bis(1,5-cyclooctadiene)diiridium(I) dichloride
1,4-di(diphenylphosphino)-butane
IrCl(1,5-cyclooctadiene)(1,4-bis(diphenylphosphino)butane)
Conditions | Yield |
---|---|
With dimethyl 2,2-diallylmalonate In dichloromethane byproducts: cyclooctadiene; to a soln. of complex in CH2Cl2 was added diphosphine, then a soln. of 3equiv of diallyl ether in CH2Cl2, the mixt. was stirred at room temp. f or 3 h (inert atm.); volatiles were removed in vac., recrystd. from CH2Cl2/n-hexane; elem. anal.; | 98% |
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
1,4-di(diphenylphosphino)-butane
A
[RuCl2(η6-p-cymene)]2(μ-dppb)
Conditions | Yield |
---|---|
In dichloromethane stirred for 4 h; filtered, solvent-removed; elem. anal.; | A 98% B 0% |
Conditions | Yield |
---|---|
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.; | 98% |
1,4-di(diphenylphosphino)-butane
(maleonitriledithilato)(1,4-bis(diphenylphosphino)butane)nickel(II)
Conditions | Yield |
---|---|
In acetone mixt. of solids NiCl2*6H2O (1 mmol) and Ph2P(CH2)4P(Ph)2 (0.42 g) in acetone stirred for 1 h; pptd. by H2O addn. with stirring; ppt. filtered off; washed (H2O, EtOH, Et2O); dried at room temp.; elem. anal.; | 98% |
dichloro(tetraethylcyclobutadiene)platinum(II)
1,4-di(diphenylphosphino)-butane
(PtCl2(C4(C2H5)4))2((C6H5)2P(CH2)4P(C6H5)2)
Conditions | Yield |
---|---|
In dichloromethane Ar-atmosphere; stirring Pt-complex with 0.5 equiv. of phosphine (room temp., 5-10 h); pptn. on Et2O addn., filtration, washing (Et2O), drying (vac.); elem. anal.; | 97% |
dichloro(tetraethylcyclobutadiene)platinum(II)
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In dichloromethane Ar-atmosphere; stirring Pt-complex with equimolar amt. of phosphine (room temp., 2-3 h); pptn. on Et2O addn., standing (overnight), filtration, washing (Et2O), drying (vac.); | 97% |
1,4-di(diphenylphosphino)-butane
[Pd(o-C6H4C=NCH=CHNMe)((C6H5)2P(CH2)4P(C6H5)2-P,P)]ClO4
Conditions | Yield |
---|---|
In acetone N2-atmosphere; stirring equimolar amts. of Pd-complex and phosphine (room temp., 2 h), addn. of NaClO4, stirring for 2 h, addn. of H2O, stirringfor 4 h (pptn.); filtration, drying (vac.), recrystn. (CH2Cl2/hexane); elem. anal.; | 97% |
RuBr2(P(C6H5)3)3
1,4-di(diphenylphosphino)-butane
RuBr2(1,4-bis(diphenylphosphino)butane)(PPh3)
Conditions | Yield |
---|---|
In further solvent(s) Ar-atmosphere; equimolar amts., stirring in CH2Br2 at room temp. for 2 h; vol. reduction, pptn. on EtOH addn., collection (filtration), washing (EtOH, hexanes), drying (vac.); elem. anal.; | 97% |
tris(triphenylphosphine)ruthenium(II) chloride
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In hexane for 2h; Reflux; | 97% |
Conditions | Yield |
---|---|
Stage #1: Ru(OAc)2(CO)(PPh3)2; 1,4-di(diphenylphosphino)-butane In dichloromethane at 20℃; for 6h; Stage #2: ethylenediamine In dichloromethane at 20℃; for 2h; | 97% |
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In chloroform at 61℃; for 65h; Inert atmosphere; | 97% |
[Ru(η1-OAc)(η2-OAc)(PPh3)2(CO)]
ethylenediamine
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
Stage #1: [Ru(η1-OAc)(η2-OAc)(PPh3)2(CO)]; 1,4-di(diphenylphosphino)-butane In dichloromethane at 20℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: ethylenediamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 97% |
formaldehyd
1,4-di(diphenylphosphino)-butane
RhCl(CO)(1,4-bis(diphenylphosphino)butane)
Conditions | Yield |
---|---|
In ethanol; water for 0.5h; Inert atmosphere; Reflux; | 96.6% |
Conditions | Yield |
---|---|
In methanol; dichloromethane for 24h; Schlenk technique; Inert atmosphere; Reflux; | 96.3% |
pentacarbonyl(acetonitrile)tungsten
1,4-di(diphenylphosphino)-butane
A
{1,4-bis(diphenylphosphino)butane}tetracarbonyltungsten(0)
B
{W(CO)5}2(P(C6H5)2(CH2)4P(C6H5)2)
Conditions | Yield |
---|---|
In toluene (W(CO)5(NCMe)) and diphosphine (molar ratio: 5:1) refluxed in toluene under nitrogen (2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR; | A 4% B 96% |
In chloroform (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in CHCl3 under nitrogen (55°C, 2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR; | A 87% B 13% |
In chloroform (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in CHCl3 under nitrogen (55°C, 2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR; | A 76% B 24% |
In toluene (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in toluene under nitrogen (2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR; | A 43% B 57% |
1,4-di(diphenylphosphino)-butane
{Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}(1+)*BF4(1-)={Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}BF4
Conditions | Yield |
---|---|
In methanol; dichloromethane H2-atmosphere; stirring (room temp., 20 min), phosphine soln. (CH2Cl2) addn., stirring (2 h); evapn. (vac.); | 96% |
dichloro(1,5-cyclooctadiene)platinum(ll)
phosphoric acid monophenyl ester
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
With Ag2O In dichloromethane react. under dry N2, addn. of (C6H5)2P(CH2)4P(C6H5)2, phenyl dihydrogenphosphate (molar ratio = 1:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.; | 96% |
dichloro(1,5-cyclooctadiene)platinum(ll)
2,6-dimethylphenyl isonitrile
1,4-di(diphenylphosphino)-butane
Conditions | Yield |
---|---|
In dichloromethane; acetone under N2; successive addn. of diphosphine, isocyanide and excess of NH4PF6 to Pt-compd. dissolved in CH2Cl2 and acetone, stirring at room temp.for 2 h; evapn. of solvent to dryness under reduced pressure, extn. of residue with CH2Cl2, washing with H2O and drying over Na2SO4, concg. of soln., crystn. by addn. of Et2O; elem. anal.; | 96% |
[Pd(μ-N3)(2-(2'-thienyl)pyridine(-H))]2
1,4-di(diphenylphosphino)-butane
[Pd(N3)(2-(2'-thienyl)pyridine)]2(μ-1,4-bis(diphenylphosphino)butane)
Conditions | Yield |
---|---|
In dichloromethane (under N2 or Ar, Schlenk); CH2Cl2 soln. of ligand added to soln. of Pd-complex in CH2Cl2, stirred for 5 h; solvent removed, washed with Et2O, recrystd. from CH2Cl2-n-hexane; elem.anal.; | 96% |
The 1,4-Bis(diphenylphosphino)butane, with the CAS registry number 7688-25-7, is also known as Phosphine, 1,1'-(1,4-butanediyl)bis(1,1-diphenyl-. It belongs to the product categories of Phosphines; Ligand; Phosphine Ligands; Synthetic Organic Chemistry. Its EINECS registry number is 231-698-7. This chemical's molecular formula is C28H28P2 and molecular weight is 426.469442. Its IUPAC name is called 4-diphenylphosphanylbutyl(diphenyl)phosphane. This chemical's classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance].
Physical properties of 1,4-Bis(diphenylphosphino)butane: (1)ACD/LogP: 9.25; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.25; (4)ACD/LogD (pH 7.4): 9.25; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 2578029; (8)ACD/KOC (pH 7.4): 2578029; (9)#Freely Rotating Bonds: 9; (10)Flash Point: 299.5 °C; (11)Enthalpy of Vaporization: 78.93 kJ/mol; (12)Boiling Point: 542 °C at 760 mmHg; (13)Vapour Pressure: 2.92E-11 mmHg at 25°C.
Uses of 1,4-Bis(diphenylphosphino)butane: it can be used to produce 1,4-tetramethylene-bis(diphenylphosphine sulphide) by heating. This reaction will need reagent 0.5M S8 and solvent toluene with reaction time of 5 min. The yield is about 85%.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)P(CCCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
(2)InChI: InChI=1S/C28H28P2/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22H,13-14,23-24H2
(3)InChIKey: BCJVBDBJSMFBRW-UHFFFAOYSA-N
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